Skip to main content

Advertisement

SpringerLink
Log in

Cholinesterase and carboxylesterase inhibitors as pharmacological agents

  • Review
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Literature data and authors’ own results on the role of serine hydrolases, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), as drug targets for treatment of neurodegenerative diseases and carboxylesterase (CaE) inhibitors as modulators of CaE-hydrolysis of ester-containing drugs are analyzed. Today, a promising approach is the development of cholinesterase inhibitors with additional neuroprotective and disease-modifying properties. The developed esterase profile approach, that is, comparative assessment of the inhibitory activity against AChE, BChE, and CaE, can be used to evaluate both the main potential pharmacological effect and possible side effects of a new compound. Analysis of the esterase profile, in combination with computer modeling and assessment of radical-scavenging ability of the synthesized compounds and their potential ability to block AChE-induced β-amyloid aggregation revealed highly active multifunctional compounds for the treatment of Alzheimer’s disease: selective inhibitors of BChE and inhibitors of both cholinesterases without potential side effects associated with CaE inhibition. A number of effective and selective inhibitors of CaE, free from cholinergic side effects, were also found for modulation of the rate of hydrolytic metabolism and for rational use of ester-containing drugs.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

We’re sorry, something doesn't seem to be working properly.

Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

References

  1. J. Z. Long, B. F. Cravatt, Chem. Rev., 2011, 111, 6022; DOI: 10.1021/cr200075y.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. D. A. Bachovchin, B. F. Cravatt, Nat. Rev. Drug Discov., 2012, 11, 52; DOI: 10.1038/nrd3620.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. M. Pohanka, Biomed. Pap. Med. Fac. Univ. Palacky Olomouc Czech Repub., 2011, 155, 219; DOI: 10.5507/bp.2011.036.

    Article  CAS  PubMed  Google Scholar 

  4. J. Massoulie, L. Pezzementi, S. Bon, E. Krejci, F.-M. Vallette, Prog. Neurobiol., 1993, 41, 31; DOI: 10.1016/0301-0082 (93) 90040-y.

    Article  CAS  PubMed  Google Scholar 

  5. G. Matthews, Annu. Rev. Neurosci., 1996, 19, 219; DOI: 10.1146/annurev.ne.19.030196.001251.

    Article  CAS  PubMed  Google Scholar 

  6. I. Wessler, C. J. Kirkpatrick, Br. J. Pharmacol., 2008, 154, 1558; DOI: 10.1038/bjp.2008.185.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. S. O. Bachurin, Med. Res. Rev., 2003, 23, 48; DOI: 10.1002/med.10026.

    Article  CAS  PubMed  Google Scholar 

  8. N. Lermontova, N. Lukoyanov, T. Serkova, E. Lukoyanova, S. Bachurin, Mol. Chem. Neuropathol., 1998, 33, 51; DOI: 10.1007/bf02815859.

    Article  CAS  PubMed  Google Scholar 

  9. H. W. Klafki, M. Staufenbiel, J. Kornhuber, J. Wiltfang, Brain, 2006, 129, 2840; DOI: 10.1093/brain/awl280.

    Article  PubMed  Google Scholar 

  10. J. Rodda, J. Carter, BMJ, 2012, 344, e2986; DOI: 10.1136/bmj.e2986.

    Article  CAS  PubMed  Google Scholar 

  11. A. Martinez, A. Castro, Expert Opin. Investig. Drugs, 2006, 15, 1; DOI: 10.1517/13543784.15.1.1.

    Article  CAS  PubMed  Google Scholar 

  12. M. Allgaier, C. Allgaier, Front. Biosci., 2014, 19, 1345; DOI: 10.2741/4285.

    Article  Google Scholar 

  13. O. Lockridge, D. M. Quinn, in Comprehensive Toxicology, Ed. C. A. Mcqueen, Elsevier, Kidlington, 2010, p. 243.

  14. O. Lockridge, Pharmacol. Ther., 2015, 148, 34; DOI: 10.1016/j.pharmthera.2014.11.011.

    Article  CAS  PubMed  Google Scholar 

  15. I. Manoharan, R. Boopathy, S. Darvesh, O. Lockridge, Clin. Chim. Acta, 2007, 378, 128; DOI: 10.1016/j.cca.2006.11.005.

    Article  CAS  PubMed  Google Scholar 

  16. B. Li, E. G. Duysen, M. Carlson, O. Lockridge, J. Pharmacol. Exp. Ther., 2008, 324, 1146; DOI: 10.1124/jpet.107.133330.

    Article  CAS  PubMed  Google Scholar 

  17. E. G. Duysen, B. Li, S. Darvesh, O. Lockridge, Toxicology, 2007, 233, 60; DOI: 10.1016/j.tox.2006.11.069.

    Article  CAS  PubMed  Google Scholar 

  18. P. Masson, S. V. Lushchekina, Chem. Biol. Interact., 2016, 259, 319; DOI: 10.1016/j.cbi.2016.02.010.

    Article  CAS  PubMed  Google Scholar 

  19. Z. Radic, N. A. Pickering, D. C. Vellom, S. Camp, P. Taylor, Biochemistry, 1993, 32, 12074; DOI: 10.1021/bi00096a018.

    Article  CAS  PubMed  Google Scholar 

  20. D. C. Vellom, Z. Radic, Y. Li, N. A. Pickering, S. Camp, P. Taylor, Biochemistry, 1993, 32, 12; DOI: 10.1021/bi00052a003.

    Article  CAS  PubMed  Google Scholar 

  21. A. Saxena, A. M. Redman, X. Jiang, O. Lockridge, B. P. Doctor, Biochemistry, 1997, 36, 14642; DOI: 10.1021/bi971425.

    Article  CAS  PubMed  Google Scholar 

  22. S. D. Varfolomeev, S. V. Lushchekina, A. V. Nemukhin, A. M. Kulakova, E. D. Kots, G. F. Makhaeva, H. Delacour, O. Lockridge, P. Masson, Russ. Chem. Bull., 2016, 65, 1592; DOI: 10.1007/s11172-016-1487-8.

    Article  CAS  Google Scholar 

  23. B. Kozlikova, E. Sebestova, V. Sustr, J. Brezovsky, O. Strnad, L. Daniel, D. Bednar, A. Pavelka, M. Manak, M. Bezdeka, P. Benes, M. Kotry, A. Gora, J. Damborsky, J. Sochor, Bioinformatics, 2014, 30, 2684; DOI: 10.1093/bioinformatics/btu364.

    Article  CAS  PubMed  Google Scholar 

  24. J. L. Sussman, M. Harel, F. Frolow, C. Oefner, A. Goldman, L. Toker, I. Silman, Science, 1991, 253, 872; DOI: 10.1126/science.1678899.

    Article  CAS  PubMed  Google Scholar 

  25. S. T. Wlodek, T. W. Clark, L. R. Scott, J. A. Mccammon, J. Am. Chem. Soc., 1997, 119, 9513; DOI: 10.1021/ja971226d.

    Article  CAS  Google Scholar 

  26. A. D. Kharlamova, S. V. Lushchekina, K. A. Petrov, E. D. Kots, F. Nachon, M. Villard-Wandhammer, I. V. Zueva, E. Krejci, V. S. Reznik, V. V. Zobov, E. E. Nikolsky, P. Masson, Biochem. J., 2016, 473, 1225; DOI: 10.1042/BCJ20160084.

    Article  CAS  PubMed  Google Scholar 

  27. P. Masson, S. V. Lushchekina, Arch. Biochem. Biophys., 2016, 593, 60; DOI: 10.1016/j.abb.2016.02.010.

    Article  CAS  PubMed  Google Scholar 

  28. M. Harel, J. L. Sussman, E. Krejci, S. Bon, P. Chanal, J. Massoulie, I. Silman, Proc. Natl. Acad. Sci. USA, 1992, 89, 10827; DOI: 10.1073/pnas.89.22.10827.

    Article  CAS  PubMed  Google Scholar 

  29. P. Masson, M.-T. Froment, C. F. Bartels, O. Lockridge, Eur. J. Biochem., 1996, 235, 36; DOI: 10.1111/j.1432-1033.1996.00036.x/pdf.

    Article  CAS  PubMed  Google Scholar 

  30. P. Masson, P. Legrand, C. F. Bartels, M. T. Froment, L. M. Schopfer, O. Lockridge, Biochemistry, 1997, 36, 2266; DOI: 10.1021/bi962484a.

    Article  CAS  PubMed  Google Scholar 

  31. P. Masson, C. Clery, P. Guerra, A. Redslob, C. Albaret, P. L. Fortier, Biochem. J., 1999, 343, 361; DOI: 10.1042/bj3430361.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. P. Masson, S. Lushchekina, L. M. Schopfer, O. Lockridge, Biochem. J., 2013, 454, 387; DOI: 10.1042/BJ20130389.

    Article  CAS  PubMed  Google Scholar 

  33. W. Kalow, R. O. Davies, Biochem. Pharmacol., 1959, 1, 183; DOI: 10.1016/0006-2952(59)90097-8.

    Article  Google Scholar 

  34. S. Darvesh, D. A. Hopkins, C. Geula, Nat. Rev. Neurosci., 2003, 4, 131; DOI: 10.1038/nrn1035.

    Article  CAS  PubMed  Google Scholar 

  35. M. M. Mesulam, A. Guillozet, P. Shaw, A. Levey, E. G. Duysen, O. Lockridge, Neuroscience, 2002, 110, 627; DOI: 10.1016/s0306-4522(01)00613-3.

    Article  CAS  PubMed  Google Scholar 

  36. E. Giacobini, Neurochem. Res., 2003, 28, 515; DOI: 10.1023/a:1022869222652.

    Article  CAS  PubMed  Google Scholar 

  37. N. H. Greig, T. Utsuki, D. K. Ingram, Y. Wang, G. Pepeu, C. Scali, Q. S. Yu, J. Mamczarz, H. W. Holloway, T. Giordano, D. Chen, K. Furukawa, K. Sambamurti, A. Brossi, D. K. Lahiri, Proc. Natl. Acad. Sci. USA, 2005, 102, 17213; DOI: 10.1073/pnas.0508575102.

    Article  CAS  PubMed  Google Scholar 

  38. E. Giacobini, Int. J. Geriatr. Psychiatry, 2003, 18, S1; DOI: 10.1002/gps.935.

    Article  PubMed  Google Scholar 

  39. S. Darvesh, A. M. Leblanc, I. R. Macdonald, G. A. Reid, V. Bhan, R. J. Macaulay, J. D. Fisk, Chem. Biol. Interact., 2010, 187, 425; DOI: 10.1016/j.cbi.2010.01.037.

    Article  CAS  PubMed  Google Scholar 

  40. C. G. Ballard, N. H. Greig, A. L. Guillozet-Bongaarts, A. Enz, S. Darvesh, Curr. Alzheimer Res., 2005, 2, 307; DOI: 10.2174/1567205054367838.

    Article  CAS  PubMed  Google Scholar 

  41. R. M. Lane, S. G. Potkin, A. Enz, Int. J. Neuropsycho pharmacol., 2006, 9, 101; DOI: 10.1017/S1461145705005833.

    Article  CAS  Google Scholar 

  42. Y. Furukawa-Hibi, T. Alkam, A. Nitta, A. Matsuyama, H. Mizo guchi, K. Suzuki, S. Moussaoui, Q. S. Yu, N. H. Greig, T. Nagai, K. Yamada, Behav. Brain Res., 2011, 225, 222; DOI: 10.1016/j.bbr.2011.07.035.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  43. I. R. Macdonald, K. Rockwood, E. Martin, S. Darvesh, J. Alzheimers Dis., 2014, 42, 379; DOI: 10.3233/JAD-140219.

    Article  CAS  PubMed  Google Scholar 

  44. S. Darvesh, R. Walsh, R. Kumar, A. Caines, S. Roberts, D. Magee, K. Rockwood, E. Martin, Alzheimer Dis. Assoc. Disord., 2003, 17, 117.

    Article  CAS  PubMed  Google Scholar 

  45. S. Darvesh, G. A. Reid, Chem. Biol. Interact., 2016, 259, 307; DOI: 10.1016/j.cbi.2016.04.022.

    Article  CAS  PubMed  Google Scholar 

  46. M. K. Ross, J. A. Crow, J. Biochem. Mol. Toxicol., 2007, 21, 187; DOI: 10.1002/jbt.20178.

    Article  CAS  PubMed  Google Scholar 

  47. T. Imai, K. Ohura, Curr. Drug Metab., 2010, 11, 793; DOI: 10.2174/138920010794328904.

    Article  CAS  PubMed  Google Scholar 

  48. S. Jana, S. Mandlekar, P. Marathe, Curr. Med. Chem., 2010, 17, 3874; DOI: 10.2174/092986710793205426.

    Article  CAS  PubMed  Google Scholar 

  49. C. E. Wheelock, Y. Nakagawa, J. Pest. Sci., 2010, 35, 215; DOI: 10.1584/jpestics.R10-12.

    Article  Google Scholar 

  50. S. Bencharit, C. L. Morton, Y. Xue, P. M. Potter, M. R. Re dinbo, Nat. Struct. Biol., 2003, 10, 349; DOI: 10.1038/nsb919.

    Article  CAS  PubMed  Google Scholar 

  51. S. Bencharit, C. L. Morton, J. L. Hyatt, P. Kuhn, M. K. Danks, P. M. Potter, M. R. Redinbo, Chem. Biol., 2003, 10, 341; DOI: 10.1016/S1074-5521(03)00071-1.

    Article  CAS  PubMed  Google Scholar 

  52. C. D. Fleming, S. Bencharit, C. C. Edwards, J. L. Hyatt, L. Tsurkan, F. Bai, C. Fraga, C. L. Morton, E. L. Howard-Williams, P. M. Potter, M. R. Redinbo, J. Mol. Biol., 2005, 352, 165; DOI: 10.1016/j.jmb.2005.07.016.

    Article  CAS  PubMed  Google Scholar 

  53. D. Wang, L. Zou, Q. Jin, J. Hou, G. Ge, L. Yang, Acta Pharm. Sin. B, 2018, 8, 699; DOI: 10.1016/j.apsb.2018.05.005.

    Article  PubMed  PubMed Central  Google Scholar 

  54. T. Imai, M. Taketani, M. Shii, M. Hosokawa, K. Chiba, Drug Metab. Dispos., 2006, 34, 1734; DOI: 10.1124/dmd.106.009381.

    Article  CAS  PubMed  Google Scholar 

  55. R. S. Holmes, M. W. Wright, S. J. Laulederkind, L. A. Cox, M. Hosokawa, T. Imai, S. Ishibashi, R. Lehner, M. Miyazaki, E. J. Perkins, P. M. Potter, M. R. Redinbo, J. Robert, T. Satoh, T. Yamashita, B. Yan, T. Yokoi, R. Zechner, L. J. Maltais, Mamm. Genome, 2010, 21, 427; DOI: 10.1007/s00335-010-9284-4.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  56. M. Hosokawa, Molecules, 2008, 13, 412; DOI: 10.3390/molecules13020412.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  57. T. Satoh, M. Hosokawa, Biomol. Ther., 2009, 17, 335; DOI: 10.4062/biomolther.2009.17.4.335.

    Article  CAS  Google Scholar 

  58. J. L. Staudinger, C. Xu, Y. J. Cui, C. D. Klaassen, Expert Opin. Drug Metab. Toxicol., 2010, 6, 261; DOI: 10.1517/17425250903483215.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  59. D. Yang, J. Yang, D. Shi, D. Xiao, Y. T. Chen, C. Black, R. Deng, B. Yan, J. Lipid. Res., 2012, 53, 529; DOI: 10.1194/jlr.M014688.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  60. S. C. Laizure, V. Herring, Z. Hu, K. Witbrodt, R. B. Parker, Pharmacotherapy, 2013, 33, 210; DOI: 10.1002/phar.1194.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  61. X. Wang, G. Wang, J. Shi, J. Aa, R. Comas, Y. Liang, H. J. Zhu, Pharmacogenomics J., 2016, 16, 220; DOI: 10.1038/tpj.2015.42.

    Article  CAS  PubMed  Google Scholar 

  62. M. Neuvonen, E. K. Tarkiainen, A. Tornio, P. Hirvensalo, T. Tapaninen, M. Paile-Hyvarinen, M. K. Itkonen, M. T. Holmberg, V. Karja, V. T. Mannisto, P. J. Neuvonen, J. Pihlajamaki, J. T. Backman, M. Niemi, Basic Clin. Pharmacol. Toxicol., 2018, 122, 341; DOI: 10.1111/bcpt.12916.

    Article  CAS  PubMed  Google Scholar 

  63. S. P. Sanghani, P. C. Sanghani, M. A. Schiel, W. F. Bosron, Protein Pept. Lett., 2009, 16, 1207; DOI: 10.2174/092986609789071324.

    Article  CAS  PubMed  Google Scholar 

  64. M. Taketani, M. Shii, K. Ohura, S. Ninomiya, T. Imai, Life Sci., 2007, 81, 924; DOI: 10.1016/j.lfs.2007.07.026.

    Article  CAS  PubMed  Google Scholar 

  65. T. Satoh, M. Hosokawa, Chem. Biol. Interact., 2006, 162, 195; DOI: 10.1016/j.cbi.2006.07.001.

    Article  CAS  PubMed  Google Scholar 

  66. P. M. Potter, R. M. Wadkins, Curr. Med. Chem., 2006, 13, 1045; DOI: 10.2174/092986706776360969.

    Article  CAS  PubMed  Google Scholar 

  67. M. J. Hatfield, P. M. Potter, Expert Opin. Ther. Pat., 2011, 21, 1159; DOI: 10.1517/13543776.2011.586339.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  68. J. M. Hatfield, M. Wierdl, R. M. Wadkins, P. M. Potter, Expert Opin. Drug Metab. Toxicol., 2008, 4, 1153; DOI: 10.1517/17425255.4.9.1153.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  69. M. J. Hatfield, L. G. Tsurkan, J. L. Hyatt, C. C. Edwards, A. Lemoff, C. Jeffries, B. Yan, P. M. Potter, J. Nat. Prod., 2013, 76, 36; DOI: 10.1021/np300628a.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  70. D. D. Wang, L. W. Zou, Q. Jin, J. Hou, G. B. Ge, L. Yang, Fitoterapia, 2017, 117, 84; DOI: 10.1016/j.fitote.2017.01.010.

    Article  CAS  PubMed  Google Scholar 

  71. G. F. Makhaeva, O. G. Serebryakova, N. P. Boltneva, T. G. Galenko, A. Y. Aksinenko, V. B. Sokolov, I. V. Martynov, Dokl. Biochem. Biophys., 2008, 423, 352; DOI: 10.1134/s1607672908060094.

    Article  CAS  PubMed  Google Scholar 

  72. R. J. Richardson, G. F. Makhaeva, Organophosphorus Compounds. Encyclopedia of Toxicology, 3rd ed., Ed. P. Wexler, Elsevier, Oxford, UK, 2014, 3, 714.

    Article  Google Scholar 

  73. G. F. Makhaeva, E. V. Radchenko, I. I. Baskin, V. A. Palyulin, R. J. Richardson, N. S. Zefirov, SAR QSAR Environ. Res., 2012, 23, 627; DOI: 10.1080/1062936X.2012.679690.

    Article  CAS  PubMed  Google Scholar 

  74. G. F. Makhaeva, E. V. Radchenko, V. A. Palyulin, E. V. Rudakova, A. Y. Aksinenko, V. B. Sokolov, N. S. Zefirov, R. J. Richardson, Chem. Biol. Interact., 2013, 203, 231; DOI: 10.1016/j.cbi.2012.10.012.

    Article  CAS  PubMed  Google Scholar 

  75. E. V. Rudakova, G. F. Makhaeva, T. G. Galenko, A. Y. Aksinenko, V. B. Sokolov, R. J. Richardson, I. V. Martynov, Dokl. Biochem. Biophys., 2012, 443, 81; DOI: 10.1134/S1607672912020068.

    Article  CAS  PubMed  Google Scholar 

  76. E. V. Radchenko, A. A. Mel'nikov, G. F. Makhaeva, V. A. Palyulin, N. S. Zefirov, Dokl. Biochem. Biophys., 2012, 443, 91; DOI: 10.1134/S1607672912020093.

    Article  CAS  PubMed  Google Scholar 

  77. G. F. Makhaeva, E. V. Rudakova, O. G. Serebryakova, A. Y. Aksinenko, S. O. Bachurin, R. J. Richardson, Russ. Chem. Bull., 2015, 64, 2203; DOI: 10.1007/s11172-015-1139-4.

    Article  CAS  Google Scholar 

  78. G. F. Makhaeva, E. V. Rudakova, O. G. Serebryakova, A. Y. Aksinenko, S. V. Lushchekina, S. O. Bachurin, R. J. Richardson, Chem. Biol. Interact., 2016, 259, 332; DOI: 10.1016/j.cbi.2016.05.002.

    Article  CAS  PubMed  Google Scholar 

  79. G. F. Makhaeva, A. Y. Aksinenko, V. B. Sokolov, O. G. Serebryakova, R. J. Richardson, Bioorg. Med. Chem. Lett., 2009, 19, 5528; DOI: 10.1016/j.bmcl.2009.08.065.

    Article  CAS  PubMed  Google Scholar 

  80. G. F. Makhaeva, A. Y. Aksinenko, V. B. Sokolov, I. I. Baskin, V. A. Palyulin, N. S. Zefirov, N. D. Hein, J. W. Kampf, S. J. Wij eyesakere, R. J. Richardson, Chem. Biol. Interact., 2010, 187, 177; DOI: 10.1016/j.cbi.2009.12.018.

    Article  CAS  PubMed  Google Scholar 

  81. N. P. Boltneva, O. G. Serebryakova, G. F. Makhaeva, I. V. Serkov, A. N. Proshin, S. O. Bachurin, Dokl. Biochem. Biophys., 2013, 451, 209; DOI: 10.1134/S160767291304011X.

    Article  CAS  PubMed  Google Scholar 

  82. A. N. Yarkevich, V. K. Brel, G. F. Makhaeva, O. G. Serebryakova, N. P. Boltneva, N. V. Kovaleva, Russ. J. Gen. Chem., 2015, 85, 1644; DOI: 10.1134/s1070363215070129.

    Article  CAS  Google Scholar 

  83. G. F. Makhaeva, N. P. Boltneva, S. V. Lushchekina, O. G. Serebryakova, T. S. Stupina, A. A. Terentiev, I. V. Serkov, A. N. Proshin, S. O. Bachurin, R. J. Richardson, Bioorg. Med. Chem., 2016, 24, 1050; DOI: 10.1016/j.bmc.2016.01.031.

    Article  CAS  PubMed  Google Scholar 

  84. E. V. Radchenko, G. F. Makhaeva, N. P. Boltneva, O. G. Serebryakova, I. V. Serkov, A. N. Proshin, V. A. Palyulin, N. S. Zefirov, Russ. Chem. Bull., 2016, 65, 570; DOI: 10.1007/s11172-016-1339-6.

    Article  CAS  Google Scholar 

  85. G. F. Makhaeva, T. P. Trofimova, N. P. Boltneva, O. G. Serebryakova, E. V. Rudakova, A. N. Proshin, S. O. Bachurin, Russ. Chem. Bull., 2016, 65, 1341; DOI: 10.1007/s11172-016-1459-z.

    Article  CAS  Google Scholar 

  86. G. F. Makhaeva, S. V. Lushchekina, N. P. Boltneva, V. B. Sokolov, V. V. Grigoriev, O. G. Serebryakova, E. A. Vikhareva, A. Y. Aksinenko, G. E. Barreto, G. Aliev, S. O. Bachurin, Sci. Rep., 2015, 5, 13164; DOI: 10.1038/srep13164.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  87. G. F. Makhaeva, S. V. Lushchekina, N. P. Boltneva, O. G. Serebryakova, E. V. Rudakova, A. A. Ustyugov, S. O. Bachurin, A. V. Shchepochkin, O. N. Chupakhin, V. N. Charushin, R. J. Richardson, Bioorg. Med. Chem., 2017, 25, 5981; DOI: 10.1016/j.bmc.2017.09.028.

    Article  CAS  PubMed  Google Scholar 

  88. L. G. Tsurkan, M. J. Hatfield, C. C. Edwards, J. L. Hyatt, P. M. Potter, Chem. Biol. Interact., 2013, 203, 226; DOI: 10.1016/j.cbi.2012.10.018.

    Article  CAS  PubMed  Google Scholar 

  89. M. C. Carreiras, E. Mendes, M. J. Perry, A. P. Francisco, J. Marco-Contelles, Curr. Top. Med. Chem., 2013, 13, 1745; DOI: 10.2174/15680266113139990135.

    Article  CAS  PubMed  Google Scholar 

  90. S. O. Bachurin, E. V. Bovina, A. A. Ustyugov, Med. Res. Rev., 2017, 37, 1186; DOI: 10.1002/med.21434.

    Article  CAS  PubMed  Google Scholar 

  91. Y. Huang, L. Mucke, Cell, 2012, 148, 1204; DOI: 10.1016/j.cell.2012.02.040.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  92. A. Agis-Torres, M. Solhuber, M. Fernandez, J. M. Sanchez-Montero, Curr. Neuropharmacol., 2014, 12, 2; DOI: 10.2174/1570159X113116660047.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  93. K. S. Dias, C. Viegas, Jr., Curr. Neuropharmacol., 2014, 12, 239; DOI: 10.2174/1570159X1203140511153200.

    Article  PubMed  PubMed Central  Google Scholar 

  94. M. Rosini, E. Simoni, A. Minarini, C. Melchiorre, Neurochem. Res., 2014, 39, 1914; DOI: 10.1007/s11064-014-1250-1.

    Article  CAS  PubMed  Google Scholar 

  95. S. O. Bachurin, E. F. Shevtsova, G. F. Makhaeva, V. V. Grigoriev, N. P. Boltneva, N. V. Kovaleva, S. V. Lushchekina, P. N. Shevtsov, M. E. Neganova, O. M. Redkozubova, E. V. Bovina, A. V. Gabrelyan, V. P. Fisenko, V. B. Sokolov, A. Y. Aksinenko, V. Echeverria, G. E. Barreto, G. Aliev, Sci. Rep., 2017, 7, 45627; DOI: 10.1038/srep45627.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  96. V. B. Sokolov, G. F. Makhaeva, A. Y. Aksinenko, V. V. Grigoriev, E. F. Shevtsova, S. O. Bachurin, Russ. Chem. Bull., 2017, 66, 1821; DOI: 10.1007/s11172-017-1953-y.

    Article  CAS  Google Scholar 

  97. R. R. Ramsay, M. R. Popovic-Nikolic, K. Nikolic, E. Uliassi, M. L. Bolognesi, Clin. Transl. Med., 2018, 7, 3; DOI: 10.1186/s40169-017-0181-2.

    Article  PubMed  PubMed Central  Google Scholar 

  98. N. Guzior, A. Wieckowska, D. Panek, B. Malawska, Curr. Med. Chem., 2015, 22, 373; DOI: 10.2174/0929867321666141106122628.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  99. D. Knez, N. Coquelle, A. Pislar, S. Zakelj, M. Jukic, M. Sova, J. Mravljak, F. Nachon, X. Brazzolotto, J. Kos, J. P. Colletier, S. Gobec, Eur. J. Med. Chem., 2018, 156, 598; DOI: 10.1016/j.ejmech.2018.07.033.

    Article  CAS  PubMed  Google Scholar 

  100. A. Wieckowska, T. Wichur, J. Godyn, A. Bucki, M. Marcinkowska, A. Siwek, K. Wieckowski, P. Zareba, D. Knez, M. Gluch-Lutwin, G. Kazek, G. Latacz, K. Mika, M. Kola czkowski, J. Korabecny, O. Soukup, M. Benkova, K. Kiec-Kononowicz, S. Gobec, B. Malawska, ACS Chem. Neurosci., 2018, 9, 1195; DOI: 10.1021/acschemneuro.8b00024.

    Article  CAS  PubMed  Google Scholar 

  101. M. A. Moran, E. J. Mufson, P. Gomez-Ramos, Acta Neuropathol., 1994, 87, 284; DOI: 10.1007/BF00296744.

    Article  CAS  PubMed  Google Scholar 

  102. G. V. De Ferrari, M. A. Canales, I. Shin, L. M. Weiner, I. Silman, N. C. Inestrosa, Biochemistry, 2001, 40, 10447; DOI: 10.1021/bi0101392.

    Article  CAS  PubMed  Google Scholar 

  103. M. Bartolini, C. Bertucci, V. Cavrini, V. Andrisano, Bio chem. Pharmacol., 2003, 65, 407; DOI: 10.1016/S0006-2952(02)01514-9.

    Article  CAS  Google Scholar 

  104. N. C. Inestrosa, M. C. Dinamarca, A. Alvarez, FEBS J., 2008, 275, 625; DOI: 10.1111/j.1742-4658.2007.06238.x.

    Article  CAS  PubMed  Google Scholar 

  105. S. V. Lushchekina, E. D. Kots, D. A. Novichkova, K. A. Petrov, P. Masson, BioNanoScience, 2017, 7, 396; DOI: 10.1007/s12668-016-0375-x.

    Article  Google Scholar 

  106. M. P. Arce, M. I. Rodriguez-Franco, G. C. Gonzalez-Munoz, C. Perez, B. Lopez, M. Villarroya, M. G. Lopez, A. G. Garcia, S. Conde, J. Med. Chem., 2009, 52, 7249; DOI: 10.1021/jm900628z.

    Article  CAS  PubMed  Google Scholar 

  107. P. Camps, X. Formosa, C. Galdeano, T. Gomez, D. Munoz-Torrero, L. Ramirez, E. Viayna, E. Gomez, N. Isambert, R. Lavilla, A. Badia, M. V. Clos, M. Bartolini, F. Mancini, V. Andrisano, A. Bidon-Chanal, O. Huertas, T. Dafni, F. J. Luque, Chem. Biol. Interact., 2010, 187, 411; DOI: 10.1016/j.cbi.2010.02.013.

    Article  CAS  PubMed  Google Scholar 

  108. V. E. Semenov, I. V. Zueva, M. A. Mukhamedyarov, S. V. Lushchekina, A. D. Kharlamova, E. O. Petukhova, A. S. Mikhailov, S. N. Podyachev, L. F. Saifina, K. A. Petrov, O. A. Minnekhanova, V. V. Zobov, E. E. Nikolsky, P. Masson, V. S. Reznik, ChemMedChem, 2015, 10, 1863; DOI: 10.1002/cmdc.201500334.

    Article  CAS  PubMed  Google Scholar 

  109. M. Hebda, M. Bajda, A. Wieckowska, N. Szalaj, A. Pasieka, D. Panek, J. Godyn, T. Wichur, D. Knez, S. Gobec, B. Malawska, Molecules, 2016, 21, 410; DOI: 10.3390/molecules21040410.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  110. I. Zueva, J. Dias, S. Lushchekina, V. Semenov, M. Mukhamediarov, F. Nachon, N. Petrova, L. Nurullin, E. Nikolsky, P. Masson, K. Petrov, Neuropharmacology, 2019, 155, 131; DOI: 10.1016/j.neuropharm.2019.05.025.

    Article  CAS  PubMed  Google Scholar 

  111. E. Radi, P. Formichi, C. Battisti, A. Federico, J. Alzheimers Dis., 2014, 42, Suppl 3, S125; DOI: 10.3233/JAD-132738.

    Article  CAS  PubMed  Google Scholar 

  112. W. J. Huang, X. Zhang, W. W. Chen, Biomed. Rep., 2016, 4, 519; DOI: 10.3892/br.2016.630.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  113. M. Pohanka, Bratisl. Lek. Listy., 2018, 119, 535; DOI: 10.4149/BLL_2018_097.

    CAS  PubMed  Google Scholar 

  114. M. G. Savelieff, G. Nam, J. Kang, H. J. Lee, M. Lee, M. H. Lim, Chem. Rev., 2018; DOI: 10.1021/acs.chemrev.8b00138.

    Google Scholar 

  115. J. N. Cobley, M. L. Fiorello, D. M. Bailey, Redox Biol., 2018, 15, 490; DOI: 10.1016/j.redox.2018.01.008.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  116. P. I. Moreira, S. L. Siedlak, G. Aliev, X. Zhu, A. D. Cash, M. A. Smith, G. Perry, J. Neurol. Transm., 2005, 112, 921; DOI: 10.1007/s00702-004-0242-8.

    Article  CAS  Google Scholar 

  117. G. H. Kim, J. E. Kim, S. J. Rhie, S. Yoon, Exp. Neurobiol., 2015, 24, 325; DOI: 10.5607/en.2015.24.4.325.

    Article  PubMed  PubMed Central  Google Scholar 

  118. R. A. Floyd, K. Hensley, Neurobiol. Aging, 2002, 23, 795; DOI: 10.1016/s0197-4580(02)00019-2.

    Article  CAS  PubMed  Google Scholar 

  119. S. Chakrabarti, M. Sinha, I. G. Thakurta, P. Banerjee, M. Chattopadhyay, Curr. Med. Chem., 2013, 20, 4648; DOI: 10.2174/09298673113209990152.

    Article  CAS  PubMed  Google Scholar 

  120. M. Rosini, E. Simoni, M. Bartolini, A. Tarozzi, R. Matera, A. Milelli, P. Hrelia, V. Andrisano, M. L. Bolognesi, C. Melchiorre, Eur. J. Med. Chem., 2011, 46, 5435; DOI: 10.1016/j.ejmech.2011.09.001.

    Article  CAS  PubMed  Google Scholar 

  121. K. Lodarski, J. Jonczyk, N. Guzior, M. Bajda, J. Gladysz, J. Walczyk, M. Jelen, B. Morak-Mlodawska, K. Pluta, B. Malawska, J. Enzyme Inhib. Med. Chem., 2015, 30, 98; DOI: 10.3109/14756366.2014.889127.

    Article  CAS  PubMed  Google Scholar 

  122. M. A. Kamal, S. Shakil, M. S. Nawaz, Q. S. Yu, D. Tweedie, Y. Tan, X. Qu, N. H. Greig, CNS Neurol. Disord. Drug. Targets, 2017, 16, 820; DOI: 10.2174/1871527316666170207160606.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  123. Q. Li, H. Yang, Y. Chen, H. Sun, Eur. J. Med. Chem., 2017, 132, 294; DOI: 10.1016/j.ejmech.2017.03.062.

    Article  CAS  PubMed  Google Scholar 

  124. A. Bosak, A. Ramic, T. Smidlehner, T. Hrenar, I. Primozic, Z. Kovarik, PloS ONE, 2018, 13, e0205193; DOI: 10.1371/journal.pone.0205193.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  125. R. Ghobadian, H. Nadri, A. Moradi, S. N. A. Bukhari, M. Mahdavi, M. Asadi, T. Akbarzadeh, H. Khaleghzadeh-Ahangar, M. Sharifzadeh, M. Amini, Bioorg. Med. Chem., 2018, 26, 4952; DOI: 10.1016/j.bmc.2018.08.035.

    Article  CAS  PubMed  Google Scholar 

  126. U. Kosak, B. Brus, D. Knez, S. Zakelj, J. Trontelj, A. Pislar, R. Sink, M. Jukic, M. Zivin, A. Podkowa, F. Nachon, X. Brazzolotto, J. Stojan, J. Kos, N. Coquelle, K. Salat, J. P. Colletier, S. Gobec, J. Med. Chem., 2018, 61, 119; DOI: 10.1021/acs.jmedchem.7b01086.

    Article  CAS  PubMed  Google Scholar 

  127. D. Karlsson, A. Fallarero, G. Brunhofer, P. Guzik, M. Prinz, U. Holzgrabe, T. Erker, P. Vuorela, Eur. J. Pharm. Sci., 2012, 45, 169; DOI: 10.1016/j.ejps.2011.11.004.

    Article  CAS  PubMed  Google Scholar 

  128. V. Andrisano, M. Naldi, A. De Simone, M. Bartolini, Expert Opin. Ther. Pat., 2018, 28, 455; DOI: 10.1080/13543776.2018.1476494.

    Article  CAS  PubMed  Google Scholar 

  129. D. Dolles, M. Hoffmann, S. Gunesch, O. Marinelli, J. Moller, G. Santoni, A. Chatonnet, M. J. Lohse, H. J. Wittmann, A. Strasser, M. Nabissi, T. Maurice, M. Decker, J. Med. Chem., 2018, 61, 1646; DOI: 10.1021/acs.jmedchem.7b01760.

    Article  CAS  PubMed  Google Scholar 

  130. S. Darvesh, M. K. Cash, G. A. Reid, E. Martin, A. Mitnitski, C. Geula, J. Neuropathol. Exp. Neurol., 2012, 71, 2; DOI: 10.1097/NEN.0b013e31823cc7a6.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  131. V. K. Ramanan, S. L. Risacher, K. Nho, S. Kim, S. Swaminathan, L. Shen, T. M. Foroud, H. Hakonarson, M. J. Huentelman, P. S. Aisen, R. C. Petersen, R. C. Green, C. R. Jack, R. A. Koeppe, W. J. Jagust, M. W. Weiner, A. J. Saykin, Mol. Psychiatry, 2014, 19, 351; DOI: 10.1038/mp.2013.19.

    Article  CAS  PubMed  Google Scholar 

  132. S. Darvesh, Curr. Alzheimer Res., 2016, 13, 1173; DOI: 10.2174/1567205013666160404120542.

    Article  CAS  PubMed  Google Scholar 

  133. D. R. Debay, G. A. Reid, I. R. Pottie, E. Martin, C. V. Bowen, S. Darvesh, Alzheimers Dement., 2017, 3, 166; DOI: 10.1016/j.trci.2017.01.005.

    Google Scholar 

  134. I. R. Macdonald, S. P. Maxwell, G. A. Reid, M. K. Cash, D. R. Debay, S. Darvesh, J. Alzheimers Dis., 2017, 58, 491; DOI: 10.3233/JAD-170164.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  135. W. Froestl, A. Pfeifer, A. Muhs, J. Alzheimers Dis., 2013, 34, 1; DOI: 10.3233/JAD-121729.

    Article  CAS  PubMed  Google Scholar 

  136. S. Bhattacharya, A. Maelicke, D. Montag, J. Alzheimers Dis., 2015, 46, 123; DOI: 10.3233/JAD-142421.

    Article  CAS  PubMed  Google Scholar 

  137. M. L. Bolognesi, A. Cavalli, ChemMedChem, 2016, 11, 1190; DOI: 10.1002/cmdc.201600161.

    Article  CAS  PubMed  Google Scholar 

  138. M. Singh, M. Kaur, N. Chadha, O. Silakari, Mol. Divers., 2016, 20, 271; DOI: 10.1007/s11030-015-9628-9.

    Article  CAS  PubMed  Google Scholar 

  139. E. Uliassi, F. Prati, S. Bongarzone, M.L. Bolognesi, in Design of Hybrid Molecules for Drug Development, Ed. M. Decker, Elsevier, Amsterdam, 2017, p. 259.

  140. G. F. Makhaeva, V. B. Sokolov, E. F. Shevtsova, N. V. Kovaleva, S. V. Lushchekina, N. P. Boltneva, E. V. Rudakova, A. Y. Aksinenko, P. N. Shevtsov, M. E. Neganova, L. G. Dubova, S. O. Bachurin, Pure Appl. Chem., 2017, 89, 1167; DOI: 10.1515/pac-2017-0308.

    Article  CAS  Google Scholar 

  141. G. F. Makhaeva, E. F. Shevtsova, N. V. Kovaleva, E. V. Rudakova, M. E. Neganova, L. G. Dubova, P. N. Shevtsov, A. Y. Aksinenko, V. B. Sokolov, S. O. Bachurin, Russ. Chem. Bull., 2018, 67, 2121; DOI: 10.1007/s11172-018-2338-6.

    Article  CAS  Google Scholar 

  142. J. Han, H. J. Lee, K. Y. Kim, S. J. C. Lee, J. M. Suh, J. Cho, J. Chae, M. H. Lim, ACS Chem. Neurosci., 2018, 9, 800; DOI: 10.1021/acschemneuro.7b00454.

    Article  CAS  PubMed  Google Scholar 

  143. A. Minarini, A. Milelli, E. Simoni, M. Rosini, M. Bolognesi, C. Marchetti, V. Tumiatti, Curr. Top. Med. Chem., 2013, 13, 1771; DOI: 10.2174/15680266113139990136.

    Article  CAS  PubMed  Google Scholar 

  144. M. Rosini, E. Simoni, M. Bartolini, E. Soriano, J. Marco-Contelles, V. Andrisano, B. Monti, M. Windisch, B. Hutter-Paier, D. W. Mcclymont, I. R. Mellor, M. L. Bolognesi, ChemMedChem, 2013, 8, 1276; DOI: 10.1002/cmdc.201300263.

    Article  CAS  PubMed  Google Scholar 

  145. M. L. Bolognesi, M. Bartolini, A. Tarozzi, F. Morroni, F. Lizzi, A. Milelli, A. Minarini, M. Rosini, P. Hrelia, V. Andrisano, C. Melchiorre, Bioorg. Med. Chem. Lett., 2011, 21, 2655; DOI: 10.1016/j.bmcl.2010.12.093.

    Article  CAS  PubMed  Google Scholar 

  146. D. Sabolova, P. Kristian, M. Kozurkova, J. Appl. Toxicol., 2018, 38, 1377; DOI: 10.1002/jat.3622.

    Article  CAS  PubMed  Google Scholar 

  147. A. Milelli, A. De Simone, N. Ticchi, H. H. Chen, N. Betari, V. Andrisano, V. Tumiatti, Curr. Med. Chem., 2017, 24, 3522; DOI: 10.2174/0929867324666170309123920.

    Article  CAS  PubMed  Google Scholar 

  148. V. Hepnarova, J. Korabecny, L. Matouskova, P. Jost, L. Muckova, M. Hrabinova, N. Vykoukalova, M. Kerhartova, T. Kucera, R. Dolezal, E. Nepovimova, K. Spilovska, E. Mezeiova, N. L. Pham, D. Jun, F. Staud, D. Kaping, K. Kuca, O. Soukup, Eur. J. Med. Chem., 2018, 150, 292; DOI: 10.1016/j.ejmech.2018.02.083.

    Article  CAS  PubMed  Google Scholar 

  149. K. Czarnecka, P. Szymanski, M. Girek, E. Mikiciuk-Olasik, R. Skibinski, J. Kabzinski, I. Majsterek, B. Malawska, J. Jonczyk, M. Bajda, Bioorg. Chem., 2017, 72, 315; DOI: 10.1016/j.bioorg.2017.05.003.

    Article  CAS  PubMed  Google Scholar 

  150. R. Skibinski, K. Czarnecka, M. Girek, I. Bilichowski, N. Chufarova, E. Mikiciuk-Olasik, P. Szymanski, Chem. Biol. Drug Des., 2018, 91, 505; DOI: 10.1111/cbdd.13111.

    Article  CAS  PubMed  Google Scholar 

  151. Y. Li, J. Geng, Y. Liu, S. Yu, G. Zhao, ChemMedChem, 2013, 8, 27; DOI: 10.1002/cmdc.201200355.

    Article  CAS  PubMed  Google Scholar 

  152. A. Castro, T. Castano, A. Encinas, W. Porcal, C. Gil, Bioorg. Med. Chem., 2006, 14, 1644; DOI: 10.1016/j.bmc.2005.10.012.

    Article  CAS  PubMed  Google Scholar 

  153. G. F. Makhaeva, A. N. Proshin, N. P. Boltneva, E. V. Rudakova, N. V. Kovaleva, O. G. Serebryakova, I. V. Serkov, S. O. Bachurin, Russ. Chem. Bull., 2016, 65, 1586; DOI: 10.1007/s11172-016-1486-9.

    Article  CAS  Google Scholar 

  154. V. V. Grigoriev, G. F. Makhaeva, A. N. Proshin, N. V. Kovaleva, E. V. Rudakova, N. P. Boltneva, A. V. Gabrel'yan, B. V. Lednev, S. O. Bachurin, Russ. Chem. Bull., 2017, 66, 1308; DOI: 10.1007/s11172-017-1890-9.

    Article  CAS  Google Scholar 

  155. A. Martinez, E. Fernandez, A. Castro, S. Conde, I. Rodriguez-Franco, J.-E. Banos, A. Badia, Eur. J. Med. Chem., 2000, 35, 913; DOI: 10.1016/s0223-5234(00)01166-1.

    Article  CAS  PubMed  Google Scholar 

  156. W. Porcal, P. Hernandez, M. Gonzalez, A. Ferreira, C. Olea-Azar, H. Cerecetto, A. Castro, J. Med. Chem., 2008, 51, 6150; DOI: 10.1021/jm8006432.

    Article  CAS  PubMed  Google Scholar 

  157. G. F. Makhaeva, V. V. Grigoriev, A. N. Proshin, N. V. Kovaleva, E. V. Rudakova, N. P. Boltneva, I. V. Serkov, S. O. Bachurin, Dokl. Biochem. Biophys., 2017, 477, 405; DOI: 10.1134/S1607672917060163.

    Article  CAS  PubMed  Google Scholar 

  158. N. V. Kovaleva, A. N. Proshin, E. V. Rudakova, N. P. Boltneva, I. V. Serkov, G. F. Makhaeva, Biomed. Chem. Res. and Methods, 2018, 1, e00027; DOI: 10.18097/ bmcrm00027.

    Article  Google Scholar 

  159. A. N. Proshin, I. V. Serkov, L. N. Petrova, S. O. Bachurin, Russ. Chem. Bull., 2014, 63, 1148; DOI: 10.1007/s11172-014-0563-1.

    Article  CAS  Google Scholar 

  160. G. F. Makhaeva, N. V. Kovaleva, S. V. Lushchekina, E. V. Rudakova, N. P. Boltneva, A. N. Proshin, B. V. Lednev, I. V. Serkov, S. O. Bachurin, Dokl. Biochem. Biophys., 2018, 483, 369; DOI: 10.1134/s1607672918060200.

    Article  CAS  PubMed  Google Scholar 

  161. C. T. Supuran, Molecules, 2017, 22; DOI: 10.3390/molecules22101642.

  162. S. Bag, R. Tulsan, A. Sood, H. Cho, H. Redjeb, W. Zhou, H. Levine, 3rd, B. Torok, M. Torok, Bioorg. Med. Chem. Lett., 2015, 25, 626; DOI: 10.1016/j.bmcl.2014.12.006.

    Article  CAS  PubMed  Google Scholar 

  163. L. D. Hicks, J. L. Hyatt, S. Stoddard, L. Tsurkan, C. C. Edwards, R. M. Wadkins, P. M. Potter, J. Med. Chem., 2009, 52, 3742; DOI: 10.1021/jm9001296.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  164. G. F. Makhaeva, N. P. Boltneva, N. V. Kovaleva, E. V. Rudakova, S. V. Lushchekina, A. Y. Aksinenko, V. B. Sokolov, Russ. Chem. Bull., 2018, 67, 1724; DOI: 10.1007/s11172-018-2282-5.

    Article  CAS  Google Scholar 

  165. A. Ustyugov, E. Shevtsova, S. Bachurin, Mol. Neurobiol., 2015, 52, 970; DOI: 10.1007/s12035-015-9249-4.

    Article  CAS  PubMed  Google Scholar 

  166. R. S. Doody, S. I. Gavrilova, M. Sano, R. G. Thomas, P. S. Aisen, S. O. Bachurin, L. Seely, D. Hung, I. Dimebon, Lancet, 2008, 372, 207; DOI: 10.1016/S0140-6736(08)61074-0.

    Article  CAS  PubMed  Google Scholar 

  167. P. R. Bharadwaj, K. A. Bates, T. Porter, E. Teimouri, G. Perry, J. W. Steele, S. Gandy, D. Groth, R. N. Martins, G. Verdile, Transl. Psychiatry, 2013, 3, e332; DOI: 10.1038/tp.2013.97.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  168. S. Bachurin, E. Bukatina, N. Lermontova, S. Tkachenko, A. Afanasiev, V. Grigoriev, I. Grigorieva, Y. U. Ivanov, S. Sablin, N. Zefirov, Ann. N. Y. Acad. Sci., 2006, 939, 425; DOI: 10.1111/j.1749-6632.2001.tb03654.x.

    Article  Google Scholar 

  169. A. Gluszynska, Eur. J. Med. Chem., 2015, 94, 405; DOI: 10.1016/j.ejmech.2015.02.059.

    Article  CAS  PubMed  Google Scholar 

  170. M. Bashir, A. Bano, A. S. Ijaz, B. A. Chaudhary, Molecules, 2015, 20, 13496; DOI: 10.3390/molecules200813496.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  171. K. S. Macmillan, J. Naidoo, J. Liang, L. Melito, N. S. Williams, L. Morlock, P. J. Huntington, S. J. Estill, J. Longgood, G. L. Becker, S. L. Mcknight, A. A. Pieper, J. K. De Brabander, J. M. Ready, J. Am. Chem. Soc., 2011, 133, 1428; DOI: 10.1021/ja108211m.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  172. M. R. Redinbo, P. M. Potter, Drug Discov. Today, 2005, 10, 313; DOI: 10.1016/s1359-6446(05)03383-0.

    Article  CAS  PubMed  Google Scholar 

  173. E. J. Rook, A. D. Huitema, W. Van Den Brink, J. M. Van Ree, J. H. Beijnen, Curr. Clin. Pharmacol., 2006, 1, 109; DOI: 10.2174/157488406775268219.

    Article  CAS  PubMed  Google Scholar 

  174. R. Balson, P. R. Gibson, D. Ames, P. S. Bhathal, Cns Drugs, 1995, 4, 168; DOI: 10.2165/00023210-199504030-00002.

    Article  CAS  Google Scholar 

  175. H. Jaeschke, G. J. Gores, A. I. Cederbaum, J. A. Hinson, D. Pessayre, J. J. Lemasters, Toxicol. Sci., 2002, 65, 166; DOI: 10.1093/toxsci/65.2.166.

    Article  CAS  PubMed  Google Scholar 

  176. Y.-H. Lou, J.-S. Wang, G. Dong, P.-P. Guo, D.-D. Wei, S.-S. Xie, M.-H. Yang, L.-Y. Kong, Toxicol. Res., 2015, 4, 1465; DOI: 10.1039/c5tx00096c.

    Article  CAS  Google Scholar 

  177. E. V. Shchegolkov, Ya. V. Burgart, O. G. Khudina, V. I. Saloutin, O. N. Chupakhin, Russ. Chem. Rev., 2010, 79, 31; DOI: 10.1070/RC2010v079n01ABEH004048.

    Article  CAS  Google Scholar 

  178. N. P. Boltneva, G. F. Makhaeva, N. V. Kovaleva, S. V. Lushchekina, Y. V. Burgart, E. V. Shchegol'kov, V. I. Saloutin, O. N. Chupakhin, Dokl. Biochem. Biophys., 2015, 465, 381; DOI: 10.1134/S1607672915060101.

    Article  CAS  PubMed  Google Scholar 

  179. N. P. Boltneva, G. F. Makhaeva, E. V. Shchegol'kov, Y. V. Burgart, V. I. Saloutin, Biomed. Chem. Res. and Methods, 2018, 1, e00026; DOI: 10.18097/bmcrm00026.

    Article  Google Scholar 

  180. Y. V. Burgart, A. S. Fokin, O. G. Kuzueva, O. N. Chupakhin, V. I. Saloutin, J. Fluorine Chem., 1998, 92, 101; DOI: 10.1016/s0022-1139(98)00247-4.

    Article  CAS  Google Scholar 

  181. O. G. Khudina, Y. V. Burgart, E. V. Shchegol'kov, V. I. Saloutin, O. N. Kazheva, A. N. Chekhlov, O. A. D'yachenko, Russ. J. Org. Chem., 2009, 45, 801; DOI: 10.1134/ s1070428009060013.

    Article  CAS  Google Scholar 

  182. E. V. Shchegol'kov, Y. V. Burgart, E. V. Sadchikova, V. I. Saloutin, Russ. J. Org. Chem., 2009, 45, 572; DOI: 10.1134/ s1070428009040174.

    Article  CAS  Google Scholar 

  183. A. V. Nemukhin, B. L. Grigorenko, S. V. Lushchekina, S. D. Varfolomeev, Russ. Chem. Rev., 2012, 81, 1011; DOI: 10.1070/RC2012v081n11ABEH004311.

    Article  CAS  Google Scholar 

  184. P. Bar-On, C. B. Millard, M. Harel, H. Dvir, A. Enz, J. L. Sussman, I. Silman, Biochemistry, 2002, 41, 3555; DOI: 10.1021/bi020016x.

    Article  CAS  PubMed  Google Scholar 

  185. M. Harel, D. M. Quinn, H. K. Nair, I. Silman, J. L. Sussman, J. Am. Chem. Soc., 1996, 118, 2340; DOI: 10.1021/ja952232h.

    Article  CAS  Google Scholar 

  186. O. G. Khudina, E. V. Shchegol'kov, Y. V. Burgart, M. I. Kodess, O. N. Kazheva, A. N. Chekhlov, G. V. Shilov, O. A. Dyachenko, V. I. Saloutin, O. N. Chupakhin, J. Fluorine Chem., 2005, 126, 1230; DOI: 10.1016/j.jfluchem.2005.06.001.

    Article  CAS  Google Scholar 

  187. E. V. Shchegol’kov, E. V. Sadchikova, Ya. V. Burgart, V. I. Saloutin, Russ. Chem. Bull., 2008, 57, 612; DOI: 10.1007/s11172-008-0096-6.

    Article  Google Scholar 

  188. E. V. Shchegol’kov, A. E. Ivanova, Y. V. Burgart, V. I. Saloutin, J. Heterocycl. Chem., 2013, 50, E80; DOI: 10.1002/jhet.1068.

    Article  CAS  Google Scholar 

  189. E. V. Shchegol’kov, G. F. Makhaeva, N. P. Boltneva, S. V. Lushchekina, O. G. Serebryakova, E. V. Rudakova, N. V. Kovaleva, Y. V. Burgart, V. I. Saloutin, O. N. Chupakhin, S. O. Bachurin, R. J. Richardson, Bioorg. Med. Chem., 2017, 25, 3997; DOI: 10.1016/j.bmc.2017.05.045.

    Article  CAS  PubMed  Google Scholar 

  190. E. V. Rudakova, N. P. Boltneva, G. F. Makhaeva, Bull. Exp. Biol. Med., 2011, 152, 73; DOI: 10.1007/s10517-011-1457-y.

    Article  CAS  PubMed  Google Scholar 

  191. E. V. Rudakova, G. F. Makhaeva, T. G. Galenko, A. Y. Aksinenko, V. B. Sokolov, I. V. Martynov, Dokl. Biochem. Biophys., 2013, 449, 87; DOI: 10.1134/S1607672913020099.

    Article  CAS  PubMed  Google Scholar 

  192. G. F. Makhaeva, E. V. Rudakova, A. Y. Aksinenko, V. B. Sokolov, R. J. Richardson, Phosphorus Sulfur Silicon Relat. Elem., 2016, 191, 1589; DOI: 10.1080/10426507. 2016.1216423.

    Article  CAS  Google Scholar 

  193. G. R. Mukhamadieva, N. P. Boltneva, T. G. Galenko, V. B. Sokolov, T. A. Epishina, G. F. Makhaeva, Pharm. Chem. J. (Engl. Transl.), 2012, 46, 461; DOI: 10.1007/s11094-012-0825-x.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyi proezd, 142432, Chernogolovka, Moscow Region, Russian Federation

    G. F. Makhaeva, E. V. Rudakova, N. V. Kovaleva, S. V. Lushchekina, N. P. Boltneva & A. N. Proshin

  2. N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 119334, Moscow, Russian Federation

    S. V. Lushchekina

  3. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620990, Ekaterinburg, Russian Federation

    E. V. Shchegolkov, Ya. V. Burgart & V. I. Saloutin

Authors
  1. G. F. Makhaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. V. Rudakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. V. Kovaleva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. V. Lushchekina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. P. Boltneva
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. N. Proshin
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. E. V. Shchegolkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Ya. V. Burgart
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. V. I. Saloutin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. F. Makhaeva.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 0967–0984, May, 2019.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Makhaeva, G.F., Rudakova, E.V., Kovaleva, N.V. et al. Cholinesterase and carboxylesterase inhibitors as pharmacological agents. Russ Chem Bull 68, 967–984 (2019). https://doi.org/10.1007/s11172-019-2507-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-019-2507-2

Key words

Search

Navigation